Dyestuffs and their production.



. ,New. or, Im r d t s and Their iPliqductlona f wh ch the, following is a' Spe ification. v k

NIT D sTATEs PAT NT OFFICE.

HERBERT LEYINS'ITEINIAND-JAMES BADDILEY, OF BL ACKLEY, MANCHESTER, ENG- LAND A S STGKORS TO LEVINSTEI N LIMITED, 0! MANCHESTEB,ENGLAZND.

nmwum AND 151mm PRODUCTION.

No Drawing.

To all whom it may concern: H I

Be it known that we, HERBERT LEVINSTEIN, M. Sc., Ph. D., and JAMES BADDILEY, B. 80., both subjects of the King of Great Britain and Ireland, and]: both residents of Black ley, Manchester, in .thecounty of Lancaster, England, have invented new and useful This" invention. consists in producing. val; uable az o ,dyestufils..ebyjglgoombining diaz o bodies with esters of-naplithol sulfonic acid glycins produced'as described in our British specification No. 118717 of 191,0. These substances have thefollowing general formula 7 scan where R representsan residue and n may be the numeral *1 or 2.

The following are examples of how this on unomcoocm.

and an excess of sodium carbonate sufiicient to keep the reaction mixture alkaline.

Specification of Letters Patent.

Application filed January 21, 1911. Serial No. 603,868.

same shade.

Patented Feb. 4,1913.

yields orthoanisidin and the ethyl ester of 7-am1no-1-glycin -8- naph'thol -3.6- disulfonic acid. It dissolves in concentrated sulfuric acid with a bluish-red color which on the addition of water gives. a solution of the It is readily soluble in water with a bluish-red color, turning 'yellower on the addition of caustic soda. It is insoluble in alcohol, ether and benzene.

Example 2: 93 parts. of benzidin are tetrazotized in the usual way with 69 parts sodium nitrite and 350 parts of hydrochloric acid 27 Tw. To this tetrazo solution is added an aqueous solution of 76 parts of salicylic acid and 200 parts sodium carbonate. The mixture is well stirred .for

, about an hour and 174 parts of the ethyl ester of 2-glycin-8-haphthol-6-sulfonate of sodium of the following constitution are then run in. When combination is completed, the dyestuff is isolated in the usual manner. It possesses the following constitution i coon where B stands for the diphenyl residue. It dyes cotton in brown shades of good fastness to light acids and alkalis. It is readily soluble in water with a reddish brown color, turning slightly redder on the addition of caustic soda. It dissolves in concentrated sulfuric acid with .a bluishviolet color which first becomes redder, and

'dition' of Water.

nitrite. This diazo'body is. then run into A is obtained. It dyescotton in bright in-- .an aqueous solution of 32.5 partsof ethyl I cmco.umoqminncamwomamm and dyes cotton in blue shades of good fastness to light. It. dissolves in concentrated sulfuric acid'With-a green color which gives a blue violet pr ate 'on theaddition of water. soluble-in7w'ater-with 4 ng' greener" on the addii da'. is insoluble in al.- cohol, ether'or'henzene. Instead of combining the dyestufi intermediate product in stitution ester of 2-glycin-5-naphthol-7-sulfonic acid of the following formula with sufiicient sodium carbonate to keep the reaction alkiline. The disazo dyest-ufiz' so ,formed is precipitated. from the reaction mixture bytthe-addition of salt, dried and ground.

example directly with. the 'ethyl ester of 2-glycin5-naphthol-7 sulfonic acid above mentioned it jmay be first combined with a Itpossesses the following. con

further molecule of a suitable/middle component such'as Cleves'acid, and this product may then be re-diazotized and combined {with' the above named glycin "ester. In this way a trisazo dyestufi of the'following'for m m:

es'fo f excellent. fastness to light. 'nocntratedsulfuricacid with a green b cks olntionlgiving a blue precipitateon the addition of Water, It is soluble .fin water withan-indigo blue color which is Juiichanged on the addition of caustic soda.

It'is insoluble alcohol ether, or benzene.

A very similard estulit' is obtained if the twomolecules of. gloves acid in the. above example are replaced by two molecules of alphanaphthylamin, but the paraminoacetanilid must then be replacedby a substance containing a sulfonic acid group such as for instance anilin metasul'fonic acid.

Example 4': The intermediate compound Y obtained by cbuplingthe diazo compound derived from 319 parts-of 1-amino-.8-naph and dyes cotton directly inblue shades of 6H thol-3 .6'-disu lfonic acid with "143' parts of alphana hthvla'min is' .diazotized with 6.9 parts 0 sodium' nitrite, andztlle requisite amount of hydrochloric acid. The dia'zo compound so obtained then. combined with 32.5parts of ethyl ester of 2-glycin-5- naphthol-7-sulfonicacid ofthe following constitution I in the resence of an excess of alkali. The dyestu so obtained has the following formula concentrated sulfuric acid with an olive excellent fastness to light. It dissolves in green color which on the addition of water gives first a blue precipitate and finall a 2. A20 dyestufls produced by combining reddish violet precipitate. It is rea 1ly diazo bodies with esters of naphthol sulfonic soluble in water with a blue color turning acid glycins which dyestuffs have the folviolet on the addition of caustic soda, and lowing general formula is insoluble in alcohol, ether or benzene. (303m) In all the above examples, in lace of the RooccHmH C1oHs-nN:NA ethyl esters of a naphthol su fonic acid 011 glycin other esters such as the methyl ester where R represents an organic residue,

n a numeral less than three and A an aromatic radical, and which dyestufis on reduction yield an ester of an amino glycin naphthol sulfonic acid and are soluble in Water and in concentrated sulfuric acid and are insoluble in alcohol, ether and benzene. In witness whereof we have hereunto set our hands in the presence of two subscribing witnesses.

HERBERT LEVINSTEIN. JAMES BADDILEY. Witnesses:

WILLIAM GEO. HEYs, JOHN V. CONWELL.

may be employed.

The above an typical examples of how this invention may be carried into efiect. We do not bind ourselves to these examples for it is obvious to one skilled in the art that analogous dyestuffs may be prepared by combining other diazo compounds in addition to those described above with the es ters of a naphthol sulfonic acid glycin.

We claim 1. The production of azo dyestufis by combining diazo bodies with the esters of naphthol sulfonic acid gl cins, substantially as hereinbefore describe 

